Hydrochloric Acid → (1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-(3,4-dihydro-1H-isoquinolin-2-yl)-methanone

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A solution of [4-(3,4-dihydro-1H-isoquinoline-2-carbonyl)-6,8-dimethoxy-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester (79 mg, 0.17 mmol) in 3 mL of EtOAc was stirred at room temperature, and 2 mL of HCl (3.2 M in EtOAc) was added. After stirring at room temperature overnight (deprotection is typically complete after 4-8 hours) the solvent was removed under reduced pressure and the residue was triturated with ether to give 75 mg of product as the HCl salt. H1-NMR (DMSO): δ, 8.42 (br s, 1H), 7.18 (m, 4H), 6.60 (m, 2H), 4.65 (br s, 2H), 4.27 (m, 2H), 3.98 (br s, 3H), 3.80 (s, 3H), 3.39 (m, 3H), 3.86 (m, 2H), [Note: Rotamers observed.] MS: APCI (M+H) calc'd for C22H23N3O3+H 378.4; found 378.2.

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